Huang Yan, Pan Liwei, Chang Yanling, Liang Xiaoqin, Hou Ping, Ren Chenyang, Xu Weifeng, Yang Ruiyun, Li Jun, Liu Buming
State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Collaborative Innovation Center for Guangxi Ethnic Medicine, School of Chemistry and Pharmaceutical Science, Guangxi Normal University, Guilin, 541004, China; Guangxi Key Laboratory of Tradtitional Chinese Medicine Quality Standards, Guangxi Institute of Chinese Traditional Medical & Pharmaceutical Science, Nanning, 530022, China.
State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Collaborative Innovation Center for Guangxi Ethnic Medicine, School of Chemistry and Pharmaceutical Science, Guangxi Normal University, Guilin, 541004, China.
Phytochemistry. 2023 Apr;208:113606. doi: 10.1016/j.phytochem.2023.113606. Epub 2023 Feb 1.
Twelve undescribed megastigmane glycosides, streilicifolosides A-L (1-12), together with 8 known analogues (13-21) were isolated from the leaves of Streblus ilicifolius (S.Vidal) Corner. Their plannar structures were elucidated using extensive NMR spectroscopic methods (1D and 2D-NMR spectroscopy), and HRESIMS spectroscopic data analyses. The absolute configurations of the undescribed compounds were determined by the glucose-induced shift-trend, calculated and experimental circular dichroism spectroscopy. All the compounds were tested for inhibitory effects on the production of NO in LPS-treated RAW264.7 cells, and streilicifoloside E and platanionoside D exhibited potent anti-inflammatory activity comparable to that of the positive control, with IC values of 26.33 and 21.84 μM, respectively. Furthermore, these two compounds markedly decreased the secretion of PGE2 and TNF-α and inhibited the expression of COX‒2, iNOS and NF-κB/p65 in LPS-induced RAW264.7 cells in a dose-dependent manner. In addition, the structure-activity relationships of the isolates were also discussed. The results suggest that streilicifoloside E and platanionoside D could be used as potential candidates for the development of new anti-inflammatory agents.
从毛叶鹊肾树（Streblus ilicifolius (S.Vidal) Corner）的叶子中分离出12个未描述的巨大戟烷糖苷，即鹊肾叶苷A-L（1-12），以及8个已知类似物（13-21）。通过广泛的核磁共振光谱方法（一维和二维核磁共振光谱）以及高分辨电喷雾电离质谱（HRESIMS）光谱数据分析阐明了它们的平面结构。通过葡萄糖诱导的位移趋势、计算和实验圆二色光谱确定了未描述化合物的绝对构型。测试了所有化合物对脂多糖（LPS）处理的RAW264.7细胞中一氧化氮（NO）产生的抑制作用，鹊肾叶苷E和悬铃木苷D表现出与阳性对照相当的强效抗炎活性，IC值分别为26.33和21.84μM。此外，这两种化合物显著降低了前列腺素E2（PGE2）和肿瘤坏死因子-α（TNF-α）的分泌，并以剂量依赖的方式抑制了LPS诱导的RAW264.7细胞中环氧合酶-2（COX-2）、诱导型一氧化氮合酶（iNOS）和核因子κB/p65（NF-κB/p65）的表达。此外，还讨论了分离物的构效关系。结果表明，鹊肾叶苷E和悬铃木苷D可作为开发新型抗炎药物的潜在候选物。
